Bolewood Group

A holding company and innovation lab.

We build things. We wait. We tend.

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What We Do

Bolewood Group is a holding company and innovation lab.

We build and operate independent software products.

We incubate ideas patiently.

We do selective advisory work where our experience is directly useful.

We are not a fund.

We are not an agency.

We don't pursue growth for its own sake.

How We Think

We care deeply about what happens after something is built.

Time is the primary ingredient in anything worthwhile — in products, in relationships, in trust, and in learning. We try to structure our work so time is an ally, not an enemy.

We'd rather create value than capture it. When value compounds outward — to users, partners, teams, and communities — durability follows naturally.

We believe patience is a competitive advantage, optionality is a form of kindness, and that most good things are grown slowly, not engineered all at once.

We build. We wait. We tend.

Founder

Anthony Showalter

Anthony Showalter

Founder

Bolewood Group was founded by Anthony Showalter, a software entrepreneur who has spent two decades building, running, and selling technology companies.

Anthony has founded multiple venture-backed software businesses, including Haiku and Pear Deck, both serving the education market. He's worked across the full lifecycle — from first prototype to exit to what comes after.

Today, his focus is on building and stewarding a small number of software products, alongside selective advisory and board work.

Portfolio

Bolewood Group operates a small portfolio of independently branded products. Each product has its own mission, roadmap, and user base.

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Launch timeline to be announced.

Advisory

Bolewood Group engages in select advisory and board work where our operating experience is directly relevant. This work is intentionally selective and capacity-constrained.

Contact

For general inquiries, privacy questions, or existential musings.

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